We say it a lot over here at Traveler: Americans are really bad at taking vacation. So much so that in 2017, we left 705 million vacation days on the table, the U.S. Travel Association reported. Think of all the walking tours, island naps, and life-changing meals that were missed! And while we always urge you to take all of your days—be they five or 25—we don't always practice what we preach, either. Thankfully, we've since learned the error of our ways—but we could all use the reminder that we're actually devaluing our salary by leaving those days behind. We tapped the keeper of our vacation days, Traveler's director of editorial operations Paulie Dibner, and contributor Cassie Shortsleeve to chat about vacation guilt, how to ask for time off, what to do when you have unlimited vacation, and what to actually do when you get it.